CN114605471A - Platinum complexes with 1, 2-substituted benzyldiphosphine ligands for the catalytic alkoxycarbonylation of ethylenically unsaturated compounds - Google Patents

Platinum complexes with 1, 2-substituted benzyldiphosphine ligands for the catalytic alkoxycarbonylation of ethylenically unsaturated compounds Download PDF

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CN114605471A
CN114605471A CN202111495002.9A CN202111495002A CN114605471A CN 114605471 A CN114605471 A CN 114605471A CN 202111495002 A CN202111495002 A CN 202111495002A CN 114605471 A CN114605471 A CN 114605471A
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butene
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杨寄
R·杰克斯代尔
M·贝勒
R·弗兰克
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    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
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    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
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    • C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
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    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
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    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
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    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/828—Platinum

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Abstract

Platinum complexes having 1, 2-substituted benzyldiphosphine ligands are disclosed for catalyzing the alkoxycarbonylation of ethylenically unsaturated compounds.

Description

Platinum complexes with 1, 2-substituted benzyldiphosphine ligands for the catalytic alkoxycarbonylation of ethylenically unsaturated compounds
Technical Field
The invention relates to platinum complexes with 1, 2-substituted benzyldiphosphine ligands for catalyzing the alkoxycarbonylation of ethylenically unsaturated compounds.
Background
The alkoxycarbonylation of ethylenically unsaturated compounds is an increasingly important process. Alkoxycarbonylation is understood to mean the reaction of an ethylenically unsaturated compound (for example an olefin) with carbon monoxide and an alcohol in the presence of a metal or metal complex and a ligand, to give the corresponding ester:
Figure BDA0003400440930000011
scheme 1: general reaction equation for the alkoxycarbonylation of ethylenically unsaturated compounds
WO 2011/083305A 1 describes a process for the alkoxycarbonylation. The complexes described therein have, in addition to the ligand, palladium as central atom.
Palladium has the disadvantage of being expensive.
Disclosure of Invention
The object of the invention is to provide novel complexes which have a metal as central atom which is less expensive than palladium. In addition, the complexes should also achieve good conversions in the alkoxycarbonylation.
This object is achieved by the complexes according to claim 1.
Complexes comprising Pt and compounds of formula (I)
Figure BDA0003400440930000021
Wherein
R1、R2、R3、R4Each independently of the others from- (C)1-C12) Alkyl, - (C)3-C12) -cycloalkyl, - (C)3-C12) -heterocycloalkyl, - (C)6-C20) -aryl, - (C)6-C20) -a heteroaryl group;
the group R1、R2、R3、R4Is- (C) having at least 6 ring atoms6-C20) -a heteroaryl group;
and
if R is1、R2、R3、R4Is- (C)1-C12) Alkyl, - (C)3-C12) -cycloalkyl, - (C)3-C12) -heterocycloalkyl, - (C)6-C20) -aryl or- (C)6-C20) Heteroaryl, they may each be independently of one another by one or more substituents selected from-(C1-C12) -alkyl, -O- (C)1-C12) -alkyl, -OH, -NH2And halogen.
Expression "(C)1-C12) Alkyl "includes both straight-chain and branched alkyl groups having from 1 to 12 carbon atoms. These are preferably (C)1-C8) -alkyl groups, more preferably (C)1-C6) -alkyl, most preferably (C)1-C4) -an alkyl group.
Expression "(C)3-C12) -cycloalkyl "includes monocyclic, bicyclic or tricyclic hydrocarbon groups having 3 to 12 carbon atoms. Preferably, these radicals are (C)5-C12) -a cycloalkyl group.
Expression "(C)3-C12) Heterocycloalkyl "includes non-aromatic, saturated or partially unsaturated cycloaliphatic radicals having from 3 to 12 carbon atoms, in which one or more of the ring carbon atoms are replaced by a heteroatom. Said- (C)3-C12) The heterocycloalkyl group preferably has 3 to 8, more preferably 5 or 6 ring atoms. In the heterocycloalkyl group, unlike the cycloalkyl group, one or more of the ring carbon atoms are replaced by a heteroatom or heteroatom-containing group. The heteroatom or the heteroatom-containing group is preferably selected from O, S, N.
Expression "(C)6-C20) Aryl "includes monocyclic or polycyclic aromatic hydrocarbon radicals having from 6 to 20 carbon atoms. These are preferably (C)6-C14) Aryl, more preferably (C)6-C10) -an aryl group.
Expression "(C)6-C20) Heteroaryl "includes monocyclic or polycyclic aromatic hydrocarbon radicals having from 6 to 20 carbon atoms, in which one or more of the carbon atoms are replaced by heteroatoms. Preferred heteroatoms are N, O and S. Said (C)6-C20) Heteroaryl groups have 6 to 20, preferably 6 to 14 and more preferably 6 to 10 ring atoms. Thus, for example, within the scope of the present invention, pyridinyl is C6-a heteroaryl group; furyl being C5-a heteroaryl group.
Is suitable forHaving at least 6 ring atoms of (C)6-C20) Heteroaryl radicals are in particular pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, benzofuranyl, indolyl, isoindolyl.
The expression "halogen" includes especially fluorine, chlorine, bromine and iodine. Fluorine and chlorine are particularly preferred.
In one embodiment, the group R1、R2、R3、R4At least two of (A) are- (C) having at least 6 ring atoms6-C20) -a heteroaryl group.
In one embodiment, said R is1And R3Each of the radicals being- (C) having at least 6 ring atoms6-C20) -a heteroaryl group.
In one embodiment, said R is1And R3Each of the groups is a 2-pyridyl group.
In one embodiment, R2And R4Is- (C)1-C12) -an alkyl group.
In one embodiment, R2And R4Is a tert-butyl group.
In one embodiment, the compound (I) has the structure (1):
Figure BDA0003400440930000031
the invention further relates to the use of the complexes according to the invention for catalyzing alkoxycarbonylation reactions.
Method comprising the following method steps:
a) initially charging an ethylenically unsaturated compound;
b) adding a complex as described above, or a compound of formula (I) and a Pt-containing species:
Figure BDA0003400440930000041
wherein
R1、R2、R3、R4Each independently of the others from- (C)1-C12) Alkyl, - (C)3-C12) -cycloalkyl, - (C)3-C12) -heterocycloalkyl, - (C)6-C20) -aryl, - (C)6-C20) -a heteroaryl group;
said R is1、R2、R3、R4At least one of the radicals being- (C) having at least 6 ring atoms6-C20) -a heteroaryl group;
and
if R is1、R2、R3、R4Is- (C)1-C12) Alkyl, - (C)3-C12) -cycloalkyl, - (C)3-C12) -heterocycloalkyl, - (C)6-C20) -aryl or- (C)6-C20) Heteroaryl, they may each be independently of one another substituted by one or more radicals selected from- (C)1-C12) -alkyl, -O- (C)1-C12) -alkyl, -OH, -NH2Halogen;
c) adding an alcohol;
d) inputting CO;
e) heating the reaction mixture from a) to d) where the ethylenically unsaturated compound is converted to an ester.
The method steps a), b), c) and d) can be carried out in any desired sequence. Typically, however, the addition of CO is carried out after the CO-reactant has been initially charged in steps a) to c). Steps d) and e) can be carried out simultaneously or one after the other. Furthermore, it is also possible to input CO in two or more steps, so that, for example, a part of the CO is first input, then the mixture is heated, and then another part of the CO is input.
The ethylenically unsaturated compound used as reactant in the process according to the invention contains one or more carbon-carbon double bonds. For the sake of simplicity, these compounds are also referred to below as olefins. The double bond may be terminal or internal.
The ethylenically unsaturated compound may contain additional functional groups in addition to the one or more double bonds. Here, the ethylenically unsaturated compound preferably contains a total of 2 to 30 carbon atoms, preferably 2 to 22 carbon atoms, more preferably 2 to 12 carbon atoms.
In one variant of the process, the ethylenically unsaturated compound does not comprise any further functional groups other than a carbon-carbon double bond.
In one variant of the process, the ethylenically unsaturated compound is selected from: ethylene, propylene, 1-butene, cis-and/or trans-2-butene, isobutylene, 1, 3-butadiene, 1-pentene, cis-and/or trans-2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, hexene, tetramethylethylene, heptene, 1-octene, 2-octene, di-n-butene, or mixtures thereof.
In one variant of the process, the ethylenically unsaturated compound is selected from: propylene, 1-butene, cis-2-butene, trans-2-butene, or mixtures thereof.
In one variant of the process, the ethylenically unsaturated compound is selected from: 1-pentene, cis-2-pentene, trans-2-pentene, 2-methyl-1-butene, 2-methyl-2-butene, 3-methyl-1-butene or mixtures thereof.
Suitable mixtures of olefinically unsaturated compounds are the so-called raffinates (raffinates) I to III. Raffinate I comprises 40% to 50% isobutene, 20% to 30% 1-butene, 10% to 20% cis-and trans-2-butene, up to 1% 1, 3-butadiene and 10% to 20% n-butane and isobutane. Raffinate II is C produced in naphtha cracking4A portion of the fractions and, after separation of isobutene from the raffinate I, consisting predominantly of the isomeric n-butenes, isobutane and n-butane. Raffinate III is C produced in naphtha cracking4A fraction of the fraction and consisting mainly of isomeric n-butenes and n-butane.
In one variant, a mixture comprising isobutene, 1-butene, cis-and trans-2-butene is used. Preferably, the mixture comprises 1-butene, cis-and trans-2-butene.
In one variant of the process, the alcohol in process step c) is selected from: methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-propanol, tert-butanol, 3-pentanol, cyclohexanol, phenol.
In one variant of the process, the alcohol in process step c) is methanol.
In one variation of the method, the Pt-containing species is selected from: platinum dichloride (PtCl)2) Platinum (II) acetylacetonate [ Pt (acac)2]Platinum (II) acetate [ Pt (OAc)2]Dichloro (1, 5-cyclooctadiene) platinum (II) [ Pt (cod) ]2Cl2]Bis (dibenzylideneacetone) platinum [ Pt (dba) ]2]Bis (acetonitrile) dichloroplatinum (II) [ Pt (CH)3CN)2Cl2]Platinum (cinnamyl) dichloride [ Pt (cinnamyl) Cl ]2]。
In one variation of the method, the Pt-containing species is selected from: platinum dichloride (PtCl)2) Platinum (II) acetylacetonate [ Pt (acac)2]Platinum (II) acetate [ Pt (OAc)2]。
In step d), the CO is preferably fed at a CO partial pressure of from 0.1 to 10MPa (1 to 100 bar), preferably from 1 to 8MPa (10 to 80 bar), more preferably from 2 to 6MPa (20 to 60 bar).
In step e) of the process according to the invention, the reaction mixture is preferably heated to a temperature in the range of from 60 ℃ to 160 ℃, preferably in the range of from 80 to 140 ℃, more preferably in the range of from 100 to 140 ℃, thereby converting the ethylenically unsaturated compound into an ester.
Detailed Description
The present invention will be illustrated in more detail by examples hereinafter.
Conversion of 1-octene to methyl ester
Figure BDA0003400440930000061
Reaction conditions are as follows: 1-octene (1.0mmol), PtCl2(0.01mmol, 1.0 mol%), ligand: monodentate phosphine ligand (0.04mmol, 4.0 mol%), bisDentate phosphine ligand (0.02mmol, 2.0 mol%), PTSA. H2O (monohydrate of p-toluenesulfonic acid) (5.0 mol%), MeOH (2.0ml), pressure (CO): 40 bar, temperature: 120 ℃, reaction time: for 20 hours.
The reaction was carried out with the following ligands:
monodentate phosphine ligands
Figure BDA0003400440930000071
Bidentate phosphine ligands
Figure BDA0003400440930000072
The respective yields and n/iso (n/iso) selectivities are given below the ligand. Selectivity and yield were determined by gas chromatography using mesitylene as internal standard.
Of the 16 ligands used, 11 did not provide any conversion (0%). Only with one ligand (L12 ═ 1) is conversion achieved in excess of 60%. As shown by this series of experiments, the greatest conversion was achieved with the complexes of Pt and (1) according to the invention.
The price of Pt is lower than that of Pd. The object is therefore achieved by the complexes according to the invention.

Claims (13)

1. Complexes comprising Pt and compounds of formula (I)
Figure FDA0003400440920000011
Wherein
R1、R2、R3、R4Each independently of the others from- (C)1-C12) Alkyl, - (C)3-C12) -cycloalkyl, - (C)3-C12) -heterocycloalkyl, - (C)6-C20) -aryl, - (C)6-C20) -heteroAn aryl group;
the group R1、R2、R3、R4Is- (C) having at least 6 ring atoms6-C20) -a heteroaryl group;
and is
If R is1、R2、R3、R4Is- (C)1-C12) Alkyl, - (C)3-C12) -cycloalkyl, - (C)3-C12) -heterocycloalkyl, - (C)6-C20) -aryl or- (C)6-C20) Heteroaryl, they may each be independently of one another substituted by one or more radicals selected from- (C)1-C12) -alkyl, -O- (C)1-C12) -alkyl, -OH, -NH2Halogen, or a halogen substituent.
2. The complex according to claim 1, wherein said complex,
wherein the group R1、R2、R3、R4At least two of (A) are- (C) having at least 6 ring atoms6-C20) -a heteroaryl group.
3. The complex according to any one of claims 1 to 2,
wherein the group R1And R3Each is- (C) having at least 6 ring atoms6-C20) -a heteroaryl group.
4. The complex according to any one of claims 1 to 3,
wherein the group R1And R3Each is a 2-pyridyl group.
5. The complex according to any one of claims 1 to 4,
wherein R is2And R4Is- (C)1-C12) -an alkyl group.
6. The complex according to any one of claims 1 to 5,
wherein R is2And R4Is a tert-butyl group.
7. The complex according to any one of claims 1 to 6,
wherein the compound (I) has the structure (1):
Figure FDA0003400440920000021
8. method comprising the following method steps:
a) initially charging an ethylenically unsaturated compound;
b) adding a complex according to any one of claims 1 to 7, or
Compounds of formula (I) and Pt-containing materials,
Figure FDA0003400440920000031
wherein
R1、R2、R3、R4Each independently of the others from- (C)1-C12) Alkyl, - (C)3-C12) -cycloalkyl, - (C)3-C12) -heterocycloalkyl, - (C)6-C20) -aryl, - (C)6-C20) -a heteroaryl group;
the group R1、R2、R3、R4Is- (C) having at least 6 ring atoms6-C20) -a heteroaryl group;
and is provided with
If R is1、R2、R3、R4Is- (C)1-C12) Alkyl, - (C)3-C12) -cycloalkyl, - (C)3-C12) -heterocycloalkyl, - (C)6-C20) -aryl or- (C)6-C20) Heteroaryl, they may each be each otherIndependently of one or more groups selected from- (C)1-C12) -alkyl, -O- (C)1-C12) -alkyl, -OH, -NH2Halogen;
c) adding an alcohol;
d) inputting CO;
e) heating the reaction mixture from a) to d) where the ethylenically unsaturated compound is converted to an ester.
9. The method according to claim 8, wherein,
wherein the ethylenically unsaturated compound is selected from: ethylene, propylene, 1-butene, cis-and/or trans-2-butene, isobutylene, 1, 3-butadiene, 1-pentene, cis-and/or trans-2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, hexene, tetramethylethylene, heptene, 1-octene, 2-octene, di-n-butene, or mixtures thereof.
10. The method according to any one of claims 8 and 9,
wherein the alcohol in process step c) is selected from: methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-propanol, tert-butanol, 3-pentanol, cyclohexanol, phenol.
11. The method according to any one of claims 8 to 10,
wherein the alcohol in process step c) is methanol.
12. The method according to any one of claims 8 to 11,
wherein the Pt-containing material is selected from: platinum dichloride (PtCl)2) Platinum (II) acetylacetonate [ Pt (acac)2]Platinum (II) acetate [ Pt (OAc)2]Dichloro (1, 5-cyclooctadiene) platinum (II) [ Pt (cod) ]2Cl2]Bis (dibenzylideneacetone) platinum [ Pt (dba) ]2]Bis (acetonitrile) dichloroplatinum (II) [ Pt (CH)3CN)2Cl2]And (cinnamyl) platinum dichloride [ Pt (cinnamyl) Cl2]。
13. The method according to any one of claims 8 to 12,
wherein the Pt-containing material is selected from: platinum dichloride (PtCl)2) Platinum (II) acetylacetonate [ Pt (acac ]2]Platinum (II) acetate [ Pt (OAc)2]。
CN202111495002.9A 2020-12-09 2021-12-09 Platinum complexes with 1, 2-substituted benzyldiphosphine ligands for the catalytic alkoxycarbonylation of ethylenically unsaturated compounds Pending CN114605471A (en)

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